Ammonia → HCID 69759226, compound

HRID 392318Notes

Reaction equation

HRID 392318 reaction equation
C1(C2[O:12][C@H:11]3[CH2:13][C@H:14]([N:17]4[CH:22]=[CH:21][N:20]=[C:19]([C:23](OC)=[O:24])[C:18]4=[O:27])[CH2:15][O:16][C@@H:10]3[CH2:9][O:8]2)C=CC=CC=1.[NH3:28]>C(O)(=O)C.CO>[OH:12][C@@H:11]1[C@@H:10]([CH2:9][OH:8])[O:16][CH2:15][C@@H:14]([N:17]2[CH:22]=[CH:21][N:20]=[C:19]([C:23]([NH2:28])=[O:24])[C:18]2=[O:27])[CH2:13]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 69759769HCID 69759769, compound

Product 1

HCID 69759226HCID 69759226, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

In 5.0 mL of 80% aqueous solution of acetic acid was dissolved 80 mg of methyl 4-[(4aR,7S,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate. The solution was heated at 80° C. for 2 hours and then allowed to cool, and the solvent was removed under reduced pressure. The residue was diluted with 20 mL of water and washed with diethyl ether, and water was distilled off from the aqueous layer. The residue thus obtained was dissolved in 4.0 mL of methanol, and gaseous ammonia was introduced until saturation at an ice-cooled temperature. After stirring the reaction mixture at room temperature for 2 hours, the solvent was removed under reduced pressure. The residue thus obtained was purified by column chromatography [eluent: chloroform:methanl=10:1] to obtain 24 mg of 4-[(3S,5S,6R)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxamide as a solid product.

Workup

  1. temperatureto cool
  2. customthe solvent was removed under reduced pressure
  3. additionThe residue was diluted with 20 mL of water
  4. washwashed with diethyl ether, and water
  5. distillationwas distilled off from the aqueous layer
  6. customThe residue thus obtained
  7. temperaturecooled temperature
  8. customthe solvent was removed under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by column chromatography [eluent: chloroform:methanl=10:1]

Sources & evidence

ORD record
ord-e0dcfd39dd1e4020b23f701de1eeff58
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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